


Dating Advice from an Archangel

by Fluffchick



Category: Shrek (Movies), Supernatural
Genre: Canon Divergent, Fluff, Fluff and Angst, Gabriel Lives, M/M, POV Multiple, Pre-Relationship
Language: English
Status: Completed
Published: 2017-06-24
Updated: 2017-06-24
Packaged: 2018-11-18 09:12:18
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 8
Words: 3,499
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11288208
Author URL: https://archiveofourown.org/users/Fluffchick/pseuds/Fluffchick
Summary: Castiel asks his brother for dating advice.





	1. Chapter 1

Castiel sat on the bed. Hands loosely clasped, head bowed. He was in his room at the bunker. Things had been quiet for a few days. Sam and Dean were researching their next case and Castiel had time to think. 

While he had been an observer for most of his life, in recent years he had become used to activity. He often made split second decisions. Of late, those decisions were of life or death importance and sitting here with time on his hands was starting to make him uncomfortable. Castiel reflected on what his life would be like after Sam and Dean were gone. Sure he didn't spend every waking minute with them, but his life was entwined with theirs and he dreaded the day when they would no longer be.

Without realizing, Castiel spoke, "Gabriel, I wish you were here to guide me." He let out a great sigh.

"You rang, o brother of mine?" 

Castiel's head shoots up. There propped against his desk, was Gabriel. Ankles crossed casually, lollipop present, and eyebrows waggling. 

Castiel stood, "Gabriel, how? when?..." 

"Daddy dearest resurrected me. After Kevin, he decided he needed an Archangel to watch over the prophet."

"And he chose the trickster?" Castiel's eyes narrowed, as he weighed this information.

"What, with Michael and Luci caged. Raphael and I dead. He chose me to resurrect. Raphael, after all tried to take his throne." Gabriel's tone was unusually serious."I get to stay in one piece as long as I protect the prophet." The Archangel raises his hands and shrugs his shoulders. "Daddy's orders." He goes back to slurping at his sucker. "So, what's with the distress call Cassie?"

"I need some advice." Castiel lowers his eyes and rubs at the back of his neck.

"Interesting. Go on."

"Maybe we should go elsewhere, so Sam and Dean aren't bothered, " Castiel still isn't looking at his older brother.

"Oh, and the plot thickens." Gabriel snaps his fingers. "There, all taken care of. Ask away."

"Gabriel, what did you do?" Castiel is glaring at his brother now, sparks shooting from his eyes. "They better not be in danger."

"Oh relax! I just put them to sleep. They're fine!" 

Castiel isn't sure he trusts the sparkle in his brother's eyes, but he can still feel the Winchester brothers' presence in the bunker.


	2. Chapter 2

Sam wakes up disoriented. This is not an unusual occurrence. 

What is unusual is that he seems to be laying on bales of straw in a barn. Dean is a few feet away, sleeping on his own bales. Sam could swear they had just been in the bunker. He doesn't remember coming here and isn't sure how they arrived. He plunges his hands into his hair. As he sits up, a book falls to the ground. He picks it up and places it on a bale of straw without really looking at it. Getting up slowly, he looks around.

He's checking the barn's loft when he hears his brother stir.

"Sam?" He sees Dean shoot up from his makeshift bed."Sammy?"

"Up here, Dean."

"The hell, Sam? How‘d we get here?" 

Sam climbs a ladder back to the ground. "I was hoping you’d remember."

"Man, the last thing I remember is the sandwich I was eating at the bunker." The elder Winchester rubs the sleep from his eyes.

Sam shakes his head, because of course the last thing Dean remembers is food. "Well I've checked the barn out. Not much to see, just seems to be a regular barn."

"Where's baby?" Dean panics as he peeks out the door. He sees tall grass ringed by some woods, but the Impala isn't there. He doesn't even see a real road, just some parallel ruts on the ground, as if a car drove through the grass on a regular basis. He sees a paddock of horses. Maybe the ruts were created by a horse and carriage?

"So what do you think. Djinn?"

"Is this your idea of a perfect life Dean? 'Cus it sure isn't mine!" 

"Well what are we hunting then, college boy?" 

Sam takes a deep breath and pinches his nose. If Dean is calling him names, that means he is panicking or as close as Dean gets to panicked; one of them should be calm. The younger Winchester looks again for anything out of place. His eyes fall on the book he picked up earlier. He snatches it off the bale and starts reading. Sam's confusion grows. He expected a book of lore, but what he has is a children's fairy tale.

"Well Sammy?"

Sam silently hands the book to his brother. It's his turn to peer out the barn doors.

"The hell?" Dean grumbles. "Why would you bring a children's book on a hunt?"

"Beats me."

"It's a story about ogres. I didn't think ogres were real?" The elder Winchester's brows are furrowed.

"Well, we didn't think dragons existed either. Maybe it's like that?"

"Pardon, monsieurs." 

Sam and Dean spin toward the new voice. Both have guns drawn and instinctively their bodies are held angled away from the intruder, making them smaller targets. Their guns dip slightly, when they notice their target is a cat.

The cat is an orange tabby from the looks of it; it might be normal if it weren't for the fact that it was only using two feet to stand. It's feet are encased in leather boots and a black cape is draped behind it's shoulders. There was a belt with a scabbard at the cat's hip. He was holding a hat with a yellow feather in front of him. So really, not normal at all.

"I'm beginning to feel like Alice." Sam murmurs. 

"Well Alice, heads up; he has a blade!"

The cat's eyes are huge black pupils, rimmed with an emerald green. "But monsieurs, I only wish to help." The cat pleads. Paws wringing at his hat brim.


	3. Chapter 3

"Well Cassie, I'm waiting" Gabriel snaps his fingers again. Chocolates and assorted candies appear on Castiel's dresser.

"I need some advice." Castiel reiterates. Gabriel moves his hand in a winding motion as if to hurry him along.

"I would like to know how to invite someone on a date." Castiel can feel heat bloom in his cheeks and wonders if something is wrong with his vessel.

"Cassie are you blushing? " Gabriel titters.

"No," the younger angel frowns. "I don't believe so. Now, how do I proceed?"

"Cassie, why are you asking me? Why not ask the humans that keep you as a pet?"

"I am not their pet!" Storms are brewing in Castiel's cerulean gaze.

"Oh. Oh ho." Gabriel scoffs. "You want to ask one of them out? So which one? Tall, dark and dreamy? No, no doesn't seem your type. So it must be short, dark, and grumpy. Really Cas, you could do so much better!"

"Gabriel." Castiel's voice is a warning.

"All right, all right. I'll help, but why me?"

Castiel is caught off guard by the question. "Because you are the only angel I know that has been in a long term relationship." He says earnestly.

Gabriel's golden eyes hold a hint of pain as he whispers "Kali." He is quiet for a minute lost in thought and regrets.

Castiel starts babbling to fill the uncomfortable silence. "I spent the night with a woman once; well I thought she was a woman. Until she killed me... or I thought she killed me. I was human at the time. I woke up and saw Dean. Thought I was in Heaven, until I saw Sam." Castiel continues to vomit words as the Archangel gives him a bemused look. "Turns out she was a reaper. Then I thought a woman had asked me out, when she just needed a babysitter."

Gabriel is doubled over laughing. "Of course she did. Oh Cassie, you're too precious."

"So will you help me?"

"Sure, what are big brothers for?" Gabriel breathes through the last of his mirth.


	4. Chapter 4

The Winchesters are looking at each other, silently debating the merits of trusting a talking cat. Finally, Sam sees Dean shrug his shoulders. They lower their weapons.

"Help us with what exactly?" Sam queries.

The cat whips his hat back onto his head and brandishes his sword. With quick slashes and strokes, the cat disarms the brothers. 

"Ha, Ha" gloats the cat.

Sam and Dean start moving in opposite directions, enabling the cat to only see one of them at a time. The cat swivels his head, then pounces toward Sam. The tabby lands on the bales of hay and swings around, sword first. He nicks a spot in Sam's neck. Blood starts to trickle.

Dean growls as he lunges. He uses a machete he found to lop off the cat's head.

"Dean, that was the only lead we had!" Sam laments.

"Dude, he was attacking you."

"It's a flesh wound. I think I can take an eight pound cat!"

"Cat's aren't supposed to talk, Sammy."

Sam rolls his eyes, not really surprised by his brother strike first, ask questions later attitude.

The Winchester brothers take stock of their situation.

"I guess we're hunting an ogre, if the book is anything to go by." Sam muses.

"How does the book say to gank it?"

"Well it's not exactly an instruction manual, but it does mention pitchforks." Sam returns to the loft. He drops two pitchforks at Dean's feet before clambering back down the ladder.

They do a quick surveillance of the area before departing from the barn. They creep along the path into the woods, not really sure if what they are looking for is out there. Sam wonders what form the monster will take. 

They have been moving stealthily through the trees for about five minutes, when they come to a clearing. There is a shack built around a hollowed out tree trunk and what appears to be an outhouse. There is also a swamp. In the swamp appear to be ogres. The ogres are in bathing suits and frolicking as if they are in a crystal clear lake instead of a muddy, stench ridden pit.

There are five ogres in all. They look to be a family. There are two adults and three children. The ogres are not the most interesting thing in the clearing, as it turns out. To the northern most side of the swamp is a dragon. This is not a sewer dwelling, human like creature. No this is an honest to goodness scaly, winged, fire breathing behemoth. Getting ready to dive from the dragon's neck is what appears to be a donkey. The donkey is yelling "Watch this!" 

A gingerbread man walks by with a cane. His leg appears to be held on with icing.

Dean shakes his head. "I think that's Shrek and Donkey with their families."

Sam shakes his head as if to clear the scene from his view, but the sight remains the same.

"I think we're dealing with a trickster, Sammy." Dean sighs, wondering how they are going to find a trickster in this fairy tale land.


	5. Chapter 5

"That's it. That's your advice?" Castiel is pacing. "I really had hoped you would take me serious Gabriel."

"I am taking this serious!"

"Then why aren't you giving me real advice?" Castiel is shouting now.

"Cassie, that is the best advice I can give. It will work. Trust me."

Castiel slumps onto the bed.

"Why is this so important to you?" Gabriel is sitting beside him now, resting a hand on his forearm. Castiel has never seen his brother this solemn. 

"I'm not much of an angel anymore." Castiel bows his head, ashamed. "My wings are deteriorating and I am cut off from Heaven." He stands up to resume his pacing.

"I have died and been resurrected, just as you have." Castiel stops to brace his hands on the dresser. "You know as I do, that there is nothingness for an angel when we die. We are just returned to molecules." Castiel drags in a ragged breathe. "I have fallen in love with the human in my charge..."

"Cassie you know there are consequences for that. The other angels will hunt you."

"I know, but if I am human... If I am human, I may be able to stay with him!" Castiel's has tears welling in his eyes, ready to spill over.

Gabriel is stunned. An Angel of the Lord should not be bought to tears, they are meant to be emotionless creatures.  
,  
"Dean remembers one of his trips to Heaven. Our Father commanded it be so." Castiel seeks Gabriel's gaze. "Dean's Heaven is comprised of his family members, his loved ones and he has a friend that is able to travel between personal Heavens. If I am human..." Castiel sighs "If I am human, I may be able to spend an eternity with him."

"I see." The twinkle is back in Gabriel's eyes as he says "Let's get this show on the road then." He snaps his fingers.


	6. Chapter 6

Castiel finds that they have been transported to the map room, where the Winchester boys are just waking up.

"What's going on?" Dean springs from his chair. "How the hell are you here?"

"Cassie invited me." Gabriel smirks before popping his lollipop back in his mouth.

"Where did you send us?" Dean stalks toward the Archangel.

"Helllooo, Trickster, " Gabriel's finger in circling in front of his own face "I didn't send you anywhere. Just made you dream."

"Oh yeah, you just made Sam and I dream the same dream, huh?" Dean's voice is dangerously low. "And how is Sam bleeding if it was 'just a dream', huh?"

"Gabriel, you told me they were just sleeping, how is Sam injured?"

"You knew?" Dean's anger has shifted to Castiel.

"I did not know Sam would be injured, Dean!"

"Not good enough, Cas."

"Guys!" Sam's voice puts a halt to the accusations. "I'm fine. WHY is Gabriel here?"

Sam and Dean glare at Gabriel. Gabriel looks to Castiel, who is staring at Dean. When Dean looks at him, Castiel starts to speak.

"I longed to ask my brother for advice. I did not know he was alive, but when Gabriel felt my longing, he showed up."

"You wanted to ask this douchewad for advice?" Dean scoffs. "Sammy or I would be happy to help! And how is he alive?" Dean's mouth is turned down in a sure sign of anger, but Castiel can hear a thread of hurt in his voice.

He makes his tone soothing, "Our Father resurrected him to protect the prophet."

"Well then, where was he when Kevin needed him?" Dean lashes out, still not over the guilt for his role in that debacle.

"It was after Kevin that I was resurrected, you monkey!"

"Enough!" Castiel has had it. "You will be civil or you will hold your tongue!"

"Yeah!" Dean smirks.

"You too, Dean!" Sam speaks out.

"Well Cassie, maybe I should come back at a better time..."

Castiel is still staring at Dean. Sam rolls his eyes at Gabriel. Gabriel responds with a smirk as he sidles closer to Sam.

"Cas?" Dean is used to Castiel staring, but there are issues at hand.

"Dean, will you give me the pleasure of your company for dinner?" Castiel always speaks formally, but this a little much even for him.

"You want to go get something to eat?" Dean isn't sure how the conversation has shifted. 

"Yes Dean, dinner."

"Well sure, Cas. Sammy you coming?"

"Uh Dean, I'm pr-pretty sure Cas wants..." Sam stutters, "You know what? I'm good thanks." Sam sinks down onto a chair to watch the rest of the show.

"Well you don't need food, so you're not invited," Dean is back to glaring at Gabriel.

"No problem, Dean-O!" Gabriel's smirk is back. He drops into the seat beside Sam.

"Alright Cas, let's go."

"Uh Dean, don't you want to change? You have straw clinging to your clothes." Sam receives a grateful smile from Castiel for his comment.

"Huh, I guess. Maybe I should take a shower too," Dean is already on his way.

"And wear a suit!" Castiel commands, as he heads to his own room to freshen up.


	7. Chapter 7

"So Samsquatch, can you help me with my problem?" Gabriel's eyebrows shift up and down suggestively as he asks the question.

"Uh, what problem is that?"

"Why the ogre of course."

"That was a cartoon ogre."

"Well, yeah that one was, but I was hoping you could tell me if the pitchfork worked. Friend with a problem and all that." Gabriel is giving Sam a solemn look and it confuses him.

"Gabriel you're an Archangel, you can take care of anything."

"Well of course I can, Sammich. But not every being knows I'm an Archangel. Only the angels, you and Dean-O, really. And Dear old Dad"

Sam's eyebrows raise as the corners of his mouth turn down, his head bobs up and down a time or two. "Fair enough, but why didn't you just ask for help?"

Gabriel sighs as if the Sam isn't the brightest student. "What's the fun in that?"

Sam contemplates that for a half a second. "How was your way fun?!"

"Well, it was fun for me." Gabriel leers.

Sam snickers, "Well I haven't read anything about ogres, but I do remember cataloging a couple of books on 'fairy tale' lore." Sam rubs his hands in anticipation of new things to learn.

"Sammich, if you didn't attack the ogre, how did you get nicked?"

"A cat!" Dean snorts, as he walks into the room. He seems to be in a much better mood after his shower.

"You were attacked by Puss in Boots. " Gabriel gives a full bellied laugh.

"Shut up." Sam growls a little, but there is a playfulness to it.


	8. Chapter 8

Dean and Castiel pull out of the Bunker's garage. Whitesnake playing softly in the background.

"So, what's with the monkey suit?" Dean is squinting one eye.

"I had something a little classier than a diner in mind Dean." Castiel gives a small smile.

Dean seems nonplussed for a moment, but recovers quickly. "So where to then?"

"There is a French restaurant a few towns over."

"French, huh?" Dean smirks at him, but follows the directions Castiel gives to the restaurant. A comfortable silence settles in the car. As they get near the restaurant, Dean starts to fidget.

“Is something wrong Dean?” As always, Cas is tuned in to Dean’s mood.

They had arrived at Mon Ami. Dean pulls the key from the ignition and twirls the key in it’s ring. 

“Uh Cas, what did you need to ask Gabriel, that you couldn’t ask me? And if not me, what about Sam?” Dean’s voice is low.

Cas glances out his window. “I wanted advice on how to ask someone out.”

Dean smirks. “Good call not asking Sammy, he’s terrible with the ladies.”

“Uh Dean…”

“But Cas, I work with you all the time on flirting with beautiful women.”

“DEAN!” Cas is glaring at him now. Dean goes back over his words to see what he had said to upset his best friend.

“What?!” Dean glares back.

“Forget it.” Cas gets out of the car and starts walking back the way they had arrived. 

“Cas, where ya goin’?” Dean is confused. “I thought we were gonna eat?” He follows after the angel.

Cas lets out a growl. “I’ve lost my appetite.”

“You’re an angel, you don’t have an appetite.”

“Great observation, Dean.” Cas seems to be picking up the pace.

Dean grabs his arm and spins him around. Cas won’t raise his gaze from the ground, so Dean bends over until he is looking into Cas’ eyes. He straightens as Cas raises his head, never breaking eye contact. As he holds the stare, his mind is sorting and discarding details. 

Cas isn’t wearing his trench coat and that is definitely a new tie. It’s twisted, of course, Cas never seems to be able to keep a tie in order. And his suit seems to be a darker shade than normal. The French restaurant. Suddenly, Dean feels like a jerk.

“Cas?” Dean breathes quietly.”Cas, are we on a date?”

Cas’ gaze skitters away. He mumbles something that sounds suspiciously like “That was the idea.”

“Cas. I’m flattered.” Dean rocks back on his heels. “So are we going to finish our date?”

Cas’ head tilts and his eyes narrow in confusion. “You want to finish our date?” He parrots.

“Well, yeah Cas.” Dean clasps Cas’ hands in his. “I’m not really used to dating dudes, but I’m not opposed. We’re talking about me and you. And for you, I’m willing to try.”

“But Dean, what if it doesn’t work out?” Cas looks despondent.

“Cas, I don’t think that’s going to be a problem.” Dean starts pulling his date toward the restaurant. “Just remember, I don’t put out on the first date.” Dean chortles.

Cas stops walking, his brows crease. “But Dean, you always put out on the first date.”


End file.
